The upgrade itself:

Assuming you can access internet from the ESXi Server just run the following; your server should be upgraded in about 20 -30 minutes.
Note: this requires some downtime. Also, although the upgrade process will not touch the disk partition layout or the VMFS filesystem, I would recommend have a backup of the guest OSs handy.

1) Shut down all VMs

2) Put ESXi host in maintenance mode' can do either command line on esxi host as root”
vim-cmd /hostsvc/maintenance_mode_enter

Conclusion

You shouldn't have to buy the commercial supported version of the ESXi. If the existing license key is not compatible with ESXi 5.5, you may have to acquire a new free ESXi 5.5 license key. That's a fairly straight forward task.

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